Elaine May: The Perfectionist Who Revolutionized Comedy

Overview

Elaine May (born Elaine Iva Berlin in 1932) is one of the most influential yet enigmatic figures in twentieth-century comedy. As half of the legendary Nichols and May duo, she helped create the art of improvisational sketch comedy and brought it to Broadway acclaim in just a few years. Her story, as chronicled in Shawn Levy's In On the Joke, is one of meteoric rise, self-imposed exile, and a second act repeatedly frustrated by a system that both celebrated and punished her ambition. Levy profiles May as part of a generation of pioneering women comedians who entered the field without role models and created their own paths.

Plot Role in the Book

Levy dedicates an entire chapter to May — "Six: The Perfectionist" — positioning her as a central figure in the revolution of comedy in the late 1950s and early 1960s. Unlike the other women profiled, May was never strictly a stand-up comedian; her fame rested on collaborative improvisation. The book traces her from her childhood in the Yiddish theater through her partnership with Mike Nichols, and then follows the starkly divergent paths the two took after their split. Her role in the narrative is to illustrate both the creative heights possible when talent meets opportunity and the obstacles that awaited a woman who dared to demand creative control in Hollywood.

Motivations and Traits Shown Through Actions

May's driving motivation was artistic truth, not commercial success. Evidence from the book shows she was "completely disconnected from the practical world" (a quote from her manager Jack Rollins). Her perfectionism — the chapter's title — was both her greatest strength and her most damaging flaw. She would shoot scenes ten, twenty, even thirty times on the set of A New Leaf, rewriting constantly and firing staff. This obsession with getting every detail right came from a belief that comedy must be rooted in "the realities of human behavior," as she stated when defending her failed play A Matter of Position. She was also fiercely independent, dressing bohemian, smoking cigars, and going through boyfriends with little care — a new type of woman for comedy circles.

Chronological Arc

May's life unfolds in distinct phases:

• Childhood (1932–1944): Born in Philadelphia to Yiddish theater troupers, she took the stage as early as age three, playing a boy named Benny until she began to mature physically. After her father died in 1944, her mother moved the family to Chicago and later Los Angeles.
• Chicago and the Compass (early 1950s–1955): Arriving in Chicago as a single mother with little formal education, she joined the experimental Playwrights Theatre Club and then the Compass Theater, the first theater devoted entirely to comic improvisation. She led the improv workshops after Paul Sills left.
• Nichols and May (1957–1962): Partnering with Mike Nichols, she rose from cabarets to Broadway in An Evening with Mike Nichols and Elaine May, renowned for fully improvised final scenes. Critics singled her out as the sharper and more versatile comic.
• Post-Split Struggles (1962–1970): After the duo disbanded, May wrote a failed play, divorced Sheldon Harnick, and saw her directing ambitions thwarted. A Life article asked "Whatever Happened to Elaine May?".
• Directing Career (1971–1976): She directed three films: A New Leaf (1971), The Heartbreak Kid (1972), and Mikey and Nicky (1976). The first was taken from her and recut, the second was a hit, the third was a notorious production that nearly ended her career.
• Later Life (1980s–2019): She worked as an uncredited script doctor on Tootsie, Reds, and other films; reunited with Nichols for stage performances and The Birdcage; wrote plays; and won a Tony Award in 2019 for The Waverly Gallery.

Relationships

Mike Nichols

The central relationship of May's professional life. Nichols was often thought of as her "second banana" by contemporary observers. They were "hardly on speaking terms" after the split, but eventually reconciled. Nichols urged her to direct A New Leaf and later consulted on her editing. They reunited for live performances and film collaborations.

Sheldon Harnick

May married the lyricist in 1962. The marriage lasted only three months; they separated while he was in London and she in Philadelphia, divorcing soon after.

David Rubinfine

Her second husband, a psychologist who had been her therapist. The marriage lasted from 1963 until his death in 1982. They blended families and lived in a townhouse but May kept a separate writing space.

Stanley Donen

Her later life partner, the director of Singin' in the Rain. They never married but collaborated on a screenplay. Donen died in 2019.

Daughter Jeannie Berlin

May's daughter, an actress who appeared in The Heartbreak Kid and later wrote and starred in In the Spirit, which May acted in.

Key Decisions and Consequences

Theme and Symbol Connections

May embodies several key themes from In On the Joke:

Gender Discrimination in Comedy

Levy explicitly notes the "sexist resistance she faced when pursuing control as a director." The book shows that when May tried to build a career equivalent to Nichols's, the system battered her down. An agent told her the studio wouldn't give her approval over directors but would allow her to direct herself — a backhanded opportunity. Even her success was framed as novelty: critics were amazed a woman could be so versatile.

Self-Invention and Persona

May invented not only characters but a new art form. She created the "rules" of improv comedy and could transform into "a sexy starlet, a nagging Jewish mother, a pompous PTA chairlady, a little girl, or an urban sophisticate." Her offstage persona was equally constructed: bohemian, unconcerned with fashion, smoking cigars.

Persistence and Resilience

Despite repeated setbacks — a play booed on opening night, a film taken from her, being the subject of a "Whatever Happened to..." article — she kept working. She returned to Broadway in her eighties and won a Tony.

Trailblazing Legacy

May is positioned as a pioneer who "helped to create the 'rules' of improv" and whose influence pervades modern comedy. The book argues that without her, there would be no Second City, no SNL.

Censorship and Double Standards

A sketch mocking sponsor products was cut from the West Coast broadcast — one of several instances where her material was deemed too risky for television.

5 Book-Specific Questions and Answers

Q1: Why did Elaine May and Mike Nichols stop performing together? A: The book states that May wrote a failed play, A Matter of Position, which led to the end of the partnership. Nichols recalled it as "in a way the worst time in my life" because he lost both his best friend and his work.

Q2: What happened with the film A New Leaf? A: May directed, wrote, and starred in the film. She overshot the schedule by forty days and doubled the budget. The studio took the footage away and recut it, adding a happy ending. May sued to stop its release but lost. She disowned the film and refused to promote it.

Q3: How did sexism affect May's directing career? A: Levy reports that when May wanted to direct, her agent told her the studio wouldn't give her approval over other directors but would let her do it herself — an exercise in "Elaine May." After the difficult production of A New Leaf, executives called her "a fucking maniac." It would be over a decade before she directed again.

Q4: What was May's role in creating improvisational comedy? A: The book says she helped "create the 'rules' for what constituted an improv scene" and was the inventor of much of Nichols and May's material. At the Compass Theater, she conducted the improv workshops and developed the techniques later used at Second City.

Q5: What recognition did May receive late in life? A: In 2013 she received a National Medal of Arts from President Obama. In 2019 she won a Tony Award for Best Actress in a Drama for The Waverly Gallery, giving a graceful, humorous acceptance speech at age 87.

For further exploration, see the ending explained and questions and answers pages.